


Drabble Request Collection- Pennywise (1986)

by red_and_blue_sewer_circus



Series: Drabble collections [1]
Category: IT - Stephen King, It 1986
Genre: Biting, Blood, Body Horror, Breeding, Crossdressing, Double Penetration, F/M, Horror, Human/Monster Romance, Insults, Master/Slave, Mind Manipulation, Other, Tentacle Dick, Tentacle Sex, Tentacles, mention of suicide, multiple dicks
Language: English
Status: In-Progress
Published: 2019-06-09
Updated: 2019-06-09
Packaged: 2020-04-23 15:15:30
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 4
Words: 2,064
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/19153600
Author URL: https://archiveofourown.org/users/red_and_blue_sewer_circus/pseuds/red_and_blue_sewer_circus
Summary: A collection of my drabbles requested by users on Tumblr. They vary from explicit smut, to horror to sometimes a little bit of humor or fluff. Pennywise (2017), Pennywise (1990) and Rufo the clown coming soon.This collection is for the version of IT from the book. If you haven't read the book, just a fair warning:This Pennywise is more vile, cruel and obscene than either of his on screen counterparts.





	1. Chapter 1

**Author's Note:**

> The prompt that was requested will be posted under the notes for each chapter

**Notes for the Chapter:**

> “Fuck—I’m going to fill you up, and I’m going to put the plug in to keep it all inside of you.”

Funny how life works

Living in Derry for most of your life had prepared you, conditioned you to accept the impossible. Rationalize it in a way your brain could accept. That’s why, when the dissapearances started again, you remarked on how unfortunate it was and went about your day to day.

Nothing really seemed out of the ordinary until you met Mr. Bob Gray. You caught a glimpse of him and at first, thought he was a clown. Second glance revealed a man standing in the shadows across the street. He turned when he noticed you watching him and smiled, making you think of a clown once again. An almost comically large, white glove covered his hand as it waved in a wide, sweeping arc, back and forth through the air.

The second time you saw him he was dressed in a shiny silver suit with orange buttons and an electric blue tie. The same, unremarkable face greeted you with the same smile and wave. The visits came more frequently, his appearance revealing more of a clown shape until finally, Pennywise introduced itself. Who knew a god lived under the streets of Derry?

It told you many things while keeping you transfixed with those strange silver eyes. It told you about what it was. Where it came from. About how those ‘fucks’ those... ‘losers’ had smashed it's offspring to bits while they grew in their eggs. It wanted to try something new. Something that had never crossed it’s mind before. When a god asked you to birth it’s child, you didn’t say no.

Pennywise told you it would take time. In order to have the best chance at conceiving, breeding needed to take place when the peak of its waking cycle overlapped the peak of your fertility. Breeding practice, however, started immediately.

The first time, Pennywise’s clown smile contorted down into a frown of disgust. Like someone had suggested it lay with a sow in the mud. There was pain, and bruises and blood as it learned your body. It laughed, and mocked your 'human weakness’ but would change, adjust it’s technique until you started to feel pleasure instead of pain. When it mounted you, it would remain impassive, studying your face and seemed oblivious to its own pleasure. When it was time, Pennywise took you by the hand and lead you through the sewers. You went deeper than you had ever gone before, until you reached a door with a strange symbol on it. Behind the door was a massive web and the clown stripped off your robe before lifting you and carrying you over the sticky strands with ease. It mumbled to itself in a language not meant for your ears as it took position between your legs and then, it began.

This time was different than the ones before. Its twin cocks pulsed and writhed inside you, stretching you to the limits of what your body had learned to take.

Pennywise was different; it growled and slobbered as it thrust, desperate for release. Razor claws held you down against the web and you looked up into its glowing silver eyes. The clowns mouth split open into what could only be described as fang filled mandibles and you closed your eyes, trying to hold on to what was left of your sanity.

You felt the body above you grow in size, the web sank below you and you felt the tendrils inside you swelling, something that had never happened before. “Pen.. What are you doing?!” You held on to the strings of web, afraid to open your eyes as you felt the form lower close to your face. Silver lit up the darkness behind your eyelids and you felt the cold void of the deadlights as Pennywise’s voice gurgled and changed into the one you were familiar with. That pleasant, deep voice spewing filth.

“Ff… cnt.. I’m going to fuck your cunt until I cum. Fuck- I’m going to fill you up, and I’m going to put the plug in to keep it all inside of you. Make sure it sticks.”

It’s laughter turned into a deep roar of pleasure as it made good on it's promise.


	2. Chapter 2

**Notes for the Chapter:**

> “Bite me.” “If you insist.” 

Pointed fangs punctured her breast and blood filled the creature’s clown painted mouth. IT watched her face as she came undone, her taste the sweet tang of fear mixed with pain and pleasure.

She screamed, and clung to it's shoulders as she wildly bucked her hips against the crotch of the silver clown suit. Tendrils writhed against her insides, rubbing her, pushing deeper as she clenched around them in the throws of her orgasm.

“Pennywise!” Her body twitched and she sighed as she started to fall from her high. A smile of contentment spread on her lips and she planted a kiss to it's cheek. “Thank you”

It quickly pulled it's fangs from her breast, causing her to wince in pain as it turned to the side and spat out the ruined blood. No, it didn’t care for the way her taste had changed, not at all. It glared up at her and tilted it's head to the side in a silent question before pressing the bulbous clown nose against her neck and inhaling deeply.

“Your cunt throbbed when I sank my teeth into your tits. I can smell pain on your flesh but you taste like pleasure… why?" Pennywise pulled back and looked up at her. “Bite me.”

“W.. what?” Her eyes went wide with uncertainty as she studied the clown thing below her. It was impossible to tell it's true intentions most of the time.

“I said bite me.” The clown loosened it’s tie and lowered it along with the ruffles around it’s neck until a white strip of unmarked flesh was visible. “Here. As hard as you can but don’t expect to break my flesh with those blunted nubs you call teeth.”

“Why?” The clown snarled at her question. Truthfully, it had a reason. Curiosity. It wanted to know what it felt like. Why it sent pleasure flowing through her body went it was only meant to cause pain, but that was not the point. How dare she question it! The filthy creature was property. Something to pass the time and meant to obey it’s master!

A gloved hand slid up to her head and painfully gripped her hair. Pennywise growled as it shoved her face against it's bare shoulder. “Bite. Me! You fuck.”

Her body shook and it was treated to the scent of fresh fear. “Alright! Yes..If you insist.” Her lips parted and she pressed her teeth against it's cold, clammy skin


	3. Chapter 3

**Notes for the Chapter:**

> "bathwater" 

The water was warm and you sighed as the tension started to leave your body. Your head rested against the back of the tub and a wet washcloth covered your face, filling your senses with the scent of your lavender bath oils.

It had taken months for you to get over your fear of the bathroom. You started hearing rumors as soon as you moved into the house. That the former homeowner had killed herself, slit her wrists right in the very tub you now sat soaking in. Some minor research at the library had confirmed the rumors and you hadn’t looked at the tub without rubbing the insides of your wrists since then.

After months of showers, you finally decided enough was enough. Work was stressful, the whole town was on edge because of the dissapearances and you needed a soak to unwind.

Drip.. drip…

Water leaked out of the faucet in a steady rhythm causing you to nod off.

Drip drip.. pat.. drip pat pat

The change in rythm made you to frown underneath the washcloth before pulling it off your face.

A woman sat across from you, her back against the faucet and one arm slung over the edge of the bathtub. Blood dribbled from the long slash running up her arm and splashed against the tile floor

Drip pat drip

A wheezing noise came from your chest as the woman turned her cold dead eyes to yours and smiled.

“It took them days to find me. My body rotted in the water.”

Black filth spread through the water from the woman and you pulled back in disgusted horror. Decay replaced the sweet scent of lavender and as you watched, the woman’s body started to rot. Suddenly, she sat up straight in the tub and lifted her other hand up from the water. A straight razor was gripped in her corpse grey hand and she pointed it at you.

“Join me. Your body will float in the water just like mine. It’s so much better when you float.”

She threw her head back and laughed, maggots spilled from her open mouth and splashed into the water. You kicked your legs as you finally managed to scream and tried to climb over the edge of the tub, anything to get away from the horrible corpse of the woman. Fingers tightened around your ankle and pulled you back into the tub, sloshing water over the edge and silencing your scream.

“Or maybe I will keep you.”

The woman pinned you down against the back of the tub and climbed over your body. Strange silver eyes stared down at you as the corpse smiled.

“I’ll lick yer cunt!”

Her cackle reached shrill new heights as she brought a hand up to her mouth. She split two fingers and flicked her silver tongue between them right in front of your face. Orange puffs lined the length of her tongue and with another cry of horror, you lashed out. You struggled, trying to get the woman off you as you were pushed back under the water.

You came back up, sputtering clear lavender water. The bathroom was empty


	4. Chapter 4

**Notes for the Chapter:**

> "Don't kink shame me." 

'Hey hey, it’s time to play. Come and take a ride on.. Pennywise!'

Over and over the chant repeated itself in your mind until you couldn’t take it anymore.

Your boss swallowed the feeble excuse of needing to go home much easier than you were anticipating and you briefly wondered if he was hearing voices in his head as well. The chant echoed in your mind again and you grabbed your purse before practically running home. Your master was calling and you needed to answer.

You felt his overwhelming presence as soon as you walked through your front door. The air was heavy with an otherworldly, animal smell and you felt the pull on your sanity grow as you climbed up the stairs. You hesitated with your hand on the knob, taking note of the bright, silver light flooding from under the bedroom door.

“Hey hey… it’s time to play… don’t keep me fucking waiting!“ The clown’s voice made you jump and you quickly stepped into the bedroom.

The silver glow was almost blinding and you shivered as cold washed over you, shocking you back to your senses. It stood before you, formless for only a moment before it rippled and changed.

Pennywise was on his knees in the middle of your bed and smiled, stretching out his clown pained lips. He gave you an over exaggerated wink before making a suggestive motion with his hand.

"Pennywise.. what are you.. wearing?”

Instead of some variation of the now familiar clown suit, Pennywise was dressed in a silver, sheer negligee. His body kept the form of a middle aged man, not overly fat but not fit either. Orange hair covered his body, the cups for the breasts hung just a little loose around his chest and the material was pulled taut over his belly.

“What’s the matter? Don’t you like it?” Pennywise kept his smile as he ran his hands, still covered by his clown gloves up his hairy thighs. “I know you do.” The claws ripped through the gloves and carved deep gouges in his thighs as he lifted the skirt of the negligee to reveal matching silver panties packing a sizable bulge. “I can see everything in that filthy little slut mind of yours.”

Your face flushed from the insult and the clown's grin spread along with the wet spot in your panties.

“Don’t.. kink shame me.”

Pennywise threw his head back and laughed as the bulge in the panties separated and started to wriggle around obscenely.

“Bitch, you won’t even remember shame by the time I’m through with you.”


End file.
